A novel approach to synthesize pyrrolo[1,2-a]quinoxalines was developed successfully by 1,3-dipolar cycloaddition of a quinoxalinium N-ylide to alkenes in the presence of MnO2 under very convenient conditions and with moderate yields (40–52%).
References
1.
NealeR. F., FallonS. L., BoyarW. C., WasleyJ. W. F., MartinL. L., StoneG. A., GlaeserB. S. and SintonC. M., Eur. J. Pharmacol., 1987, 136, 1.
2.
MaebaI., TakeuchiT., IijimaT. and FurukawaH., J. Org. Chem., 1988, 53, 1401.
3.
MaebaI., KitaoriK., ItayaY. and ItoC., J. Chem. Soc., Perkin Trans. 1, 1990, 67.
4.
MacorJ. E., BurkhartC. A., HeymJ. H., IvesJ. L., LebelL. A., NewmanM. E., NielsenJ. A., KyanK., SchulzD. W., TorgersenL. K. and KoeB. Kenneth, J. Med. Chem., 1990, 33, 2087.
5.
CampianiG., NacciV., CorelliF. and AnziniM., Synth. Commun., 1991, 21, 1567.
6.
TaylorE. C. and HandE. S., J. Am. Chem. Soc., 1963, 85, 770.
7.
TaylorE. C. and CheesemanG W. H., J. Am. Chem. Soc., 1964, 86, 1830.
8.
CheesemanG. W. H. and TuckB., J. Chem. Soc., 1965, 3678.
9.
WeidnerC. H., MichaelsF. M., BeltmanD. J. and MontgomeryC. J., J. Org. Chem., 1991, 56, 5594.
10.
KorakasD., KimbarisA. and VarvounisG., Tetrahedron, 1996, 52, 10751.
11.
CapozziG., OttanaR., RomeoG., SindinaG., UccellaN. and ValleG., J. Chem. Res. (S), 1986, 234.
12.
SuschitzkyH., WakefieldB. J. and WhitterR. A., J. Chem. Soc., Perkin Trans. 1, 1975, 2409.
13.
KimH. S., KurasawaY., YoshiiC., MasuyamaM., TakadaA. and OkamotoY., J. Heterocycl. Chem., 1990, 27, 1115.
14.
KurasawaY., KatohR., MoriF., FukuchiM., OkamotoM., TakadaA., KimH. S. and OkamotoY, J. Heterocycl. Chem., 1992, 29, 1009.
15.
ProstakovN. S. and BatibaevO. B., Russ. Chem. Rev., 1975, 44, 748.
16.
UchidaT. and MatsumotoK., Synthesis, 1976, 209.
17.
FlitschW., in Comprehensive Heterocyclic Chemistry, eds. KatrizkyA. R. and ReesC. W., Pergamon, Oxford, 1984, vol. 4, p. 476.
18.
HuY., WeiX. and HuH., in Encyclopedia of Reagents for Organic Synthesis, ed. PaquetteL. A., Wiley, New York, 1995, vol. 7, p. 4780.
19.
WeiX., HuY., LiT. and HuH., J. Chem. Soc., Perkin Trans. 1, 1993, 2487.
20.
ZhouJ., HuY. and HuH., Synth., Commun., 1998, 28, 3397.
21.
ZhouJ., HuY. and HuH., Synthesis, 1999, 166.
22.
ZhouJ., HuY. and HuH., J. Chem. Res. (S), 1999, 136.
23.
EasleyW. K. and BahnerC. T., J. Am. Chem. Soc., 1950, 72, 3803.